Batch and continuous-flow synthesis of purine nucleoside esters catalyzed by lipase TL IM.
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| Entry | R1 | R2 | Methoda | Time | Yieldb (%) |
| 1 | NH2 | CH3 | A | 26 h | 59.1 ± 0.7(3a) |
| B | 35 min | 64.0 ± 1.1(3a) | |||
| 2 | NH2 | C11H23 | A | 26 h | 64.5 ± 0.6(3b) |
| B | 35 min | 78.4 ± 0.9(3b) | |||
| 3 | NH2 | C15H31 | A | 26 h | 63.1 ± 0.4(3c) |
| B | 35 min | 79.2 ± 1.6(3c) | |||
| 4 | NH2 | (CH2)4COOCH CH2 | A | 26 h | 60.6 ± 0.5(3d) |
| B | 35 min | 74.7 ± 0.7(3d) | |||
| 5 | OH | CH3 | A | 26 h | 58.3 ± 0.9(3e) |
| B | 35 min | 67.5 ± 0.6(3e) | |||
| 6 | OH | C11H23 | A | 26 h | 77.4 ± 0.7(3f) |
| B | 35 min | 86.1 ± 1.2(3f) | |||
| 7 | OH | C15H31 | A | 26 h | 78.6 ± 1.3(3g) |
| B | 35 min | 88.7 ± 0.9(3g) | |||
| 8 | OH | (CH2)4COOCH CH2 | A | 26 h | 73.2 ± 0.7(3h) |
| B | 35 min | 77.3 ± 1.4(3h) | |||
| 9 | Cl | CH3 | A | 26 h | 61.7 ± 0.7(3i) |
| B | 35 min | 71.4 ± 0.8(3i) | |||
| 10 | Cl | C11H23 | A | 26 h | 85.3 ± 1.3(3j) |
| B | 35 min | 93.7 ± 0.9(3j) | |||
| 11 | Cl | C15H31 | A | 26 h | 84.6 ± 0.8(3k) |
| B | 35 min | 92.9 ± 1.1(3k) | |||
| 12 | Cl | (CH2)4COOCH CH2 | A | 26 h | 72.3 ± 0.8(3l) |
| B | 35 min | 80.5 ± 1.6(3l) | |||
a
Method A: batch reactor, 5.0 mmol purine nucleoside (1) and 25.0 mmol vinyl esters (2) added to 20 mL tert-amyl alcohol in a 50 mL erlenmeyer flask, 0.870 g lipase TL IM M (catalyst reactivity: 250 IUN g−1), 26 h, 50 °C. Method B: continuous-flow reactor, feed 1, 10 mL tert-amyl alcohol contained 5.0 mmol purine nucleoside (1); feed 2, 10 mL tert-amyl alcohol contained 25.0 mmol vinyl esters (2), lipase TL IM 0.870 g (catalyst reactivity: 250 IUN g−1), flow rate 18.3 μL min−1, residence time 35 min, 50 °C.
b
Isolated yield. Yield: 100 × (actual received quantity/ideal calculated quantity). The data are presented as average ± SD of triplicate experiments.